


Maiden Voyage

by ThunderThighsMish (Voib)



Category: Supernatural
Genre: Anal Fingering, Anal Sex, BAMF Castiel (Supernatural), Cabin Boy Dean, Cock Slut Dean Winchester, Doggy Style, Dom Castiel/Sub Dean Winchester, Loss of Virginity, M/M, Olive Oil as Lube, Pirate AU, Punishment, Rough Sex, Virgin Dean Winchester
Language: English
Status: Completed
Published: 2019-02-20
Updated: 2019-02-20
Packaged: 2019-11-01 04:39:07
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 2,668
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17860451
Author URL: https://archiveofourown.org/users/Voib/pseuds/ThunderThighsMish
Summary: “Mr. Winchester, howniceof you to join us.”The deep, gravelly voice made Dean’s body tense, but he continued to stare out into the undulating sea. Dean hoped that his body language presented respect instead of cowardly fear. Dean didn’t respond to Castiel’s question.“I will see you tonight in my quarters after you have finished your duties. Do not keep me waiting.” Castiel turned away from Dean and began to walk back towards his cabin. “Everyone is dismissed,” Castiel called over his shoulder.





	Maiden Voyage

**Author's Note:**

> idk why this took me so long to write. Here's some pirate porn. 
> 
> Completely un-betaed. All mistakes are mine.

__

_**Somewhere off the coast of Tripoli, 1689.** _

Dean had seen Castiel kill a man once, and thankfully only once.

The man in question was very deserving of his death, but taking a human life was something irreversible, something _illegal_. Castiel hadn’t even flinched when he had quickly cut the man’s throat, spilling hot blood onto the deck of the ship.

Dean had been the one to clean up the mess, the dark blood staining his hands.

Dean was still new by then, still new now, so he had never expected the mild mannered Captain to be capable of such unspeakable acts. But Dean had never underestimated Captain Castiel again and made sure to get all of his duties done as soon as possible, because Castiel always sent him _looks_. Castiel seemed to stare at Dean like he was a piece of meat to be devoured. He looked allured by Dean’s body, so Dean avoided eye contact and continued to swab the ship’s deck. Desires like the ones that Captain Castiel clearly expressed were dirty, filthy and _illegal_. Or, at least, that’s the little the government had to say about people like Castiel. Dean didn’t want to disrupt the government any more than he had, being part of a pirate’s ship and all. Dean knew that the hanging’s were slow and brutal for those who were accused of being part of a ship.

· · ─────── · ⚓· ─────── · ·

Dean had finished his duties late one night. After months at sea, his sea sickness had finally caught up to him and had him hanging over the railings every five minutes. This caused him to easily fall behind on cleaning the skipper’s cabin, which caused him to be working well into the dark night. Dean finally fell into bed just as the sun had started to rise and he’d missed the morning bell.

Dean was woken by being pushed out of his hammock by Benny, one of the Captain's first mates. “Get up, cher,” the man barked gruffly.

Benny left Dean’s small cellar room and Dean realized how _screwed_ he was.

His little wrist watch said that it was nearly 12:10. At exactly 12 o'clock, the Captain requested that everyone on ship did a check in. It usually only lasted a few minutes, but everyone had to be there, rain or shine, sickness or in health.

Dean threw on the shirt he had worn yesterday and rushed to pull his leather boots on. The leather stuck on his feet and Dean fell out of his hammock while still wrestling with his shoes.

Dean pounded up the stairs and across the ship, the cool sea air whipping past his ears. Dean could see the crew lined up in front of the Captain’s cabin. Dean slowed down his run into an urgent walk and finally lined up next to Benny, hoping that the man’s large frame would hide him. Dean stared straight ahead past the Captain’s quarters and to the bow of the ship, his cheeks flushed.

_What if Castiel decided that Dean wasn’t worth of being a part of the crew? Castiel wouldn’t kill an innocent, would he?_

Dean swallowed the lump in his throat when he heard the sound of leather boots slowly walking down the deck and towards where Dean was standing. Time passed at an agonizing rate until bright blue eyes were taking up Dean’s vision.

“Mr. Winchester, how _nice_ of you to join us.”

The deep, gravelly voice made Dean’s body tense, but he continued to stare out into the undulating sea. Dean hoped that his body language presented respect instead of cowardly fear. Dean didn’t respond to Castiel’s question.

“I will see you tonight in my quarters after you have finished your duties. Do not keep me waiting.” Castiel turned away from Dean and began to walk back towards his cabin. “Everyone is dismissed,” Castiel called over his shoulder.

Dean felt woozy after the whole encounter and he dazedly began to swab the south-eastern portion of the deck, another crew mate named Alfie helping him.

· · ─────── · ⚓· ─────── · ·

Dean worked his tail off that day, thankful that his sea sickness didn’t come back. The deck was cleaner that it had ever been, the kitchen sparkled and the skipper’s gun collection, along with several other crew mate’s, were primed and ready for action. Dean felt accomplished but also like had had a cannon lead stuck in his stomach. If Dean died tonight, his brother would never know, the crew wouldn’t care and the government would be happy with one less pirate on the seas.

Dean finished his duties when the sun began to set, but decided to prolong the inevitable and grab a bite to eat from the kitchen. Benny had been placed on cook duty since he had the most experience and everyone liked his cooking the most. Tonight he had decided to make biscuits, a mutton stew and some peas.

Benny gave Dean a bowl of the mutton and Dean added the peas to it. Dean dunked the biscuit in the stew’s broth and ate quickly, his stomach grumbling.

Dean cleaned his bowl and put it back in its place before he left the kitchen and started for the northern half of the ship. The gentle swaying from the water didn’t deter Dean’s feet, but he found himself walking as slowly as possible.

Dean’s felt the crew’s eyes on him as he made his way to Castiel’s cabin, his head hung low. The crew eventually got over the spectacle and continued on with making sure the ship worked smoothly.

Dean made it to the wooden door with a grimace on his face. He knocked on the door, solidly but tentatively, until a gruff voice told him to enter.

Dean opened the door to a room he’d never been in before. The walls were covered in charts and maps of places that Dean didn’t know existed. Dean wasn’t the best at reading, but he could barely struggle through the names of some of the far off, exotic lands.

_Who would call a country ‘Paasch Eiland’ and ‘Upolu’?_

Dean wandered over to the desk in the left corner of the room. It was covered in thick papers, inkwells and small golden trinkets. Gold was sought after and Dean could tell that the gold was really mined from somewhere deep in a mountain, not a rock colored golden. Dean moved to touch an alluring golden elephant with ruby eyes that sparkled so brightly in the small room.

“ _Don’t_ touch it,” a voice snapped.

Dean’s eyes flew up to where Captain Castiel was glaring daggers at him.

“That elephant was specially made for me from a prince in India. It’s ruby eyes are encrusted with silver and if you even as much as _look_ at it, I’ll string you up from your intestines on the mast.”

Dean slowly took his hands away from the little elephant and slowly put them back down to his sides. His cheeks were hot with shame, like a child being scolded for stealing sugar.

Castiel hummed in contentment and flicked his hand towards his quarters, gesturing to Dean to follow him. Castiel slipped through the door and Dean followed as close as he could.

Through the short hallway was a lavish room filled with a carved bed frame that reached for the ceiling and a wide desk that took up the corner of the room. There was a window that stretched across the western wall and left the gentle evening sunlight pouring in.

“Take a seat, Mr. Winchester,” Castiel said, gesturing towards an old wooden chair that sat next to the bed.

Dean was quick to comply.

“I believe you understand why you’re being punished?” Castiel said with a raised brow.

“Yes, sir. I was late to the check in, the one place where you don’t tolerate tardiness.” Dean couldn’t stand to look into those intense blue eyes, so he kept his gaze poised at the wooden floor.

“Are you ready to redeem yourself?” Castiel asked, demanding an answer.

“Anything, sir, to be in your good graces again. I regret my offenses,” Dean listed, trying to convey as much emotion as he could, even if he felt like a soggy sponge.

“That’s good news, Winchester. Please stand up and turn around.”

Dean pushed himself out of his chair, feeling dizzy from the sudden blood rush, and and turned away from Captain Castiel. He slumped his shoulders in an effort to appear smaller.

Castiel’s warm hands were suddenly on Dean’s shoulders and, while Dean tried not to jump, he could feel his muscles tense. Dean clenched his eyes shut and waited for some kind of sudden impact, but it never came. The broad palms make their way down Dean’s biceps to his forearms and then to his sides. Dean tried not to laugh as they brushed over a ticklish spot.

The hands settled on Dean’s hips after feeling Dean over. And the warm weight of another human, male or otherwise, made heat stir in Dean’s belly. The sensuality made Dean realize just what was happening.

Dean was supposed to be being _punished_ right now, not being pet like a stray dog!

Of course, the hands rubbed over his hip bones, moving the draw string if his pants, and Dean let out a little breath. Never would Dean admit that it was a whimper. Dean cracked his eyes open and realized that he could see the outline of his semi hard cock in his woolen pants.

Castiel’s hands had stilled, still settled on Dean’s hips, and Dean could now feel his hot breath on his neck. The man was utterly silent and it amplified the sensation tenfold.

Castiel’s lips came down to caress Dean’s neck, just behind his ear, and Dean let out a shaky breath. After so many months at sea without a moment of privacy or a willing body and Dean was almost begging for Castiel. His cock was leaking pre into his pants, and he could feel the wet spot.

Castiel, while still confident in his actions, seemed apprehensive to go any further.

So Dean tried to get him on the right track again. Dean slowly put his hands over Castiel’s and guided him to where Dean wanted him. The feeling of a caress on Dean’s cock made it twitch in its sensitivity, and a hitched moan fell from Dean’s lips.

Castiel quickly grabbed Dean’s erection and squeezed it. “Well aren’t you promiscuous,” Castiel groaned, grinding his cock into Dean’s backside. “I bet you jack your little cock at night to the thoughts of the crew _using_ you. Maybe they’d all oil you up and leave you leaking, huh?”

“Yeah,” Dean moaned. He didn’t really know what he was saying yes to, maybe all of it, maybe nothing, but he really wanted Castiel to continue touching him.

“Why don’t you get on the bed and let me dirty you up, then?”

Dean untied his shirt and let it fall to the ground as soon as Castiel backed away from him. Dean could still feel eyes looking over his freckled shoulders and down his back. Dean moved more slowly when he pulled his boots off and removed his pants. Dean sat down on the bed and enjoyed the sensation of the feather-down mattress while he waited for Castiel to catch up with him.

Castiel didn’t undress and instead watched Dean with hooded eyes. When Dean moved to stroke his cock, Castiel snapped at him with a quick, “Do _not_ touch yourself. This is a punishment, remember?.”

Dean tried to relax the best he could while Castiel took his coat off, but he was practically vibrating out of his skin.

Castiel grabbed something out of a drawer and threw Dean a little bottle with a cork stopping the top. “What’s this?” Dean asked.

“I want you to open yourself up for me, Dean,” he answered, his voice sultry.

“O-Oh. I’ve never…” Dean swallowed, “I haven’t been with a man before.”

“My God, that’s divine,” Castiel moaned. “You’re just so— _innocent_.”

Dean simply blushed in response.

“Spread your legs a little bit— _there_.”

Dean hid his face in the mattress and naturally arched his back into any touch that Castiel was willing to give him. He felt the cold oil being poured over his hole and he flinched. Of course, Castiel quickly rubbed his fingers through the substance, making sure it was spread over Dean’s hole and taint. Castiel didn’t waste time before inserting a finger into Dean’s heat.

Dean pinched his brows together at the new sensation. It was pleasurable in a mutual way; Dean knew that Castiel liked this and thus Dean liked it too, but it still felt strange.

Castiel added another finger when Dean seemed to respond favorably to the feeling. He pushed his fingers in and searched for Dean’s prostate with probing motions.

Dean let out a breath when Castiel found the spot, and Castiel immediately focused in on it, massaging and pushing the spot until Dean became a moaning mess underneath him. Sweat was beading along his back, making the man ethereal in the light. Castiel let up after a while, withdrawing his fingers, and slicking his cock with the leftover oil.

He pulled Dean’s hips up for easier access, and brought the head of his cock to Dean’s hole. He trailed his hands down the other man’s back to get him to relax, before he was pushing his cock into the heat of Dean’s body.

Dean relaxed around him, letting him sink in slow. The sheer pressure and heat made a groan fall from Castiel’s mouth. “Good boy,” Castiel commended.

Castiel didn’t waste time before he was pulling his cock out of Dean’s heat and thrusting it back in, slowly working up a rhythm. Dean had been quiet at first, but the quicker pace that Castiel pulled, the more moans and whimpers were tumbling out of Dean’s mouth.

Dean was the first to reach the edge. “I’m gonna—come,” he said while snaking an arm under his body, grasping onto his hard cock. It didn’t take much to make him spill over his fists onto the bed sheets, making a mess.

Castiel chased his finish until he came into Dean’s heat, slowly pulling his cock out and watching the come leak out with it. He pushed two fingers back into Dean’s hole, trying to keep as much come as he could inside the man.

Dean collapsed onto the bed, sleepy from his orgasm, and dozed while Castiel found a rag to clean them off with. He wiped the worst of the stains away and rid Dean of his sweat. The man hummed in adoration for the soothing strokes of the cloth before he finally fell asleep for good.

Castiel rid himself of the rest of his clothes and climbed into bed with the man, holding his warm body close.

· · ─────── · ⚓· ─────── · ·

Dean got used to staying in the Captain’s quarters after that. He was being invited into the room every night, until he had no use for his old hammock. He much rather preferred the embrace of the strong man anyways.

The crew seemed to know what was happening between Dean and the Captain, but they didn’t bother Dean about it, other than a little teasing. Dean’s stature in the ranks had gone up seemingly overnight, as people who once viewed him to be below them showed him respect. It was strange to get used to, but Dean accepted it soon enough.

Dean had also been promoted from glorified cabin boy to secondary navigator. When the boat was washed up in a storm at sea, Dean was the one who was able to use the stars to get the boat to an island that they used as shelter. Dean knew that he still struggled to read, but he had grown up studying the stars.

Castiel still made Dean run around the ship for instructions and communications, but Dean always got repaid in the warmth of their bed that night.

**Author's Note:**

> Please leave me a comment to wake up to and a kudo :)


End file.
